Synthesis and biological properties of a 1-(6-aziridinylhexyl)-2-phenylindole, a potential fluorescence label for estrogen receptors.
2-Phenylindole derivative 8, linked to aziridine by a hexamethylene spacer group, was synthesized and tested. It binds to the estrogen receptor with an RBA-value of 4.0 (estradiol = 100). In vitro, it shows a selective cytostatic activity in hormone-dependent MCF-7 breast cancer cells (41% T/C at 10(-6) M). In vivo, it exerts a strong estrogenic effect. The binding to the estrogen receptor is largely reversible.
Erber
S
S
Institut für Pharmazie, Universität Regensburg.
Birnböck
H
H
von Angerer
E
E
D000818:Animals; D001388:Aziridines / Q000138:chemical synthesis* / Q000494:pharmacology; D001943:Breast Neoplasms / Q000473:pathology; D055598:Chemical Phenomena; D002621:Chemistry; D005260:Female; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis* / Q000494:pharmacology; D051379:Mice; D011960:Receptors, Estrogen / Q000187:drug effects*; D014407:Tumor Cells, Cultured / Q000187:drug effects / Q000473:pathology
D001388:Aziridines; D005456:Fluorescent Dyes; D007211:Indoles; D011960:Receptors, Estrogen; C067016:1-(6-aziridinylhexyl)-2-(4-hydroxyphenyl)indol-5-ol